Brookline, MA Real Estate | Brookline, MA 6+ Bedrooms Homes for Sale

Rare quarter-acre retreat in the heart of Brookline Village, this fully renovated Victorian offers 5,487 square feet of exceptional living space, a large private backyard, and the character of a historic home paired with modern luxury. Completely renovated to the studs in 2025, the six-bedroom, six-bath residence is just steps from the shops, restaurants, and Green Line in Brookline Village, minutes from Longwood, and only three miles from downtown Boston. Inside, soaring ceilings, white oak hardwood floors, and extensive custom millwork, cabinetry, built-ins, and vanities create a timeless, sophisticated interior. The chef’s kitchen features high-end appliances, including a paneled Sub-Zero refrigerator and 36-inch Wolf convection range, complemented by a butler’s pantry, dedicated coffee bar, and additional under-counter wine refrigerator. Designed for both everyday living and entertaining, the home offers expansive living, dining, and family spaces, four fireplaces, radiant heated floors, two laundry rooms, and an impressive full-height lower level. A private wellness retreat includes a dedicated gym, cedar sauna, and steam shower, while a wet bar with a full-height Sub-Zero wine refrigerator and adjoining recreation space provides an additional setting for entertaining. Two oversized decks, an outdoor gas fireplace, and hot tub extend the living space outdoors and overlook the expansive, fully fenced backyard. Behind the historic exterior, the residence has been comprehensively modernized with new-construction-level infrastructure, including all-new electrical, plumbing, and mechanical systems and five-zone central heating and cooling. A rare opportunity to enjoy substantial private outdoor space, beautifully preserved Victorian character, and the comforts of a complete modern renovation in one of Brookline’s most desirable and convenient locations. See more at 220Aspinwall.com

220 Aspinwall Ave, Brookline

Listing courtesy of Listing Agent: Christopher Roy from Listing Office: Gibson Sotheby's International Realty.

$3,200,000

8 Beds ⋅ 3 Baths ⋅ 73575010 MLS

Excellent opportunity to acquire a substantial three-family investment property in a desirable Brookline location with immediate access to Cleveland Circle and Coolidge Corner. Totaling 5,118 square feet, the building offers three exceptionally spacious apartments consisting of one two-bedroom and two three-bedroom units. Each residence features a generous and functional layout with large bedrooms, eat-in kitchens, hardwood floors, ample storage, and charming original details throughout. The property has been well maintained, including a new rubber roof installed in 2021, and offers off-street parking for multiple vehicles behind the building. Its location provides convenient access to public transportation, the Longwood Medical Area, Boston College, and the many shops, restaurants, and neighborhood amenities found throughout Brookline. All three apartments are occupied by long-term tenants on fixed leases extending through 2027, providing immediate and stable rental income for the next owner. A well-positioned Brookline multifamily asset offering substantial square footage, strong existing tenancy, and excellent long-term investment potential.

3 Strathmore Rd, Brookline

Listing courtesy of Listing Agent: Matthew Foley from Listing Office: Fenway Property Advisors.

$7,500

6 Beds ⋅ 3 Baths ⋅ 73573387 MLS

Welcome to 48 Auburn Street, a spacious and charming 6-bedroom, 2.5-bath single-family home ideally located in the heart of Brookline. Available September 1st, this distinctive residence combines generous living space with beautiful original character and an exceptionally convenient location between Coolidge Corner and Brookline Village. Inside, you’ll find gorgeous original woodwork, hardwood floors, and two decorative fireplaces that add warmth and classic Brookline charm throughout the home. The kitchen is equipped with a dishwasher, and laundry is conveniently available in the home. Enjoy additional outdoor living space on the private deck, perfect for relaxing, dining, or entertaining. A private driveway with parking for two cars is also included—a major convenience in Brookline. With six bedrooms, 2.5 bathrooms, abundant character, and easy access to restaurants, shops, parks, public transportation, Coolidge Corner, and Brookline Village, 48 Auburn Street offers a rare opportunity to rent a full single-family home in one of Brookline’s most desirable locations.

48 Auburn Street Unit 48, Brookline

Listing courtesy of Listing Agent: Marika & Associates Group from Listing Office: Hammond Residential Real Estate.

$11,750,000

6 Beds ⋅ 6 Baths ⋅ 73570794 MLS

One of Brookline’s most exceptional offerings in over a decade, this remarkable 1929 Colonial Revival estate is set on two beautifully landscaped acres in the town’s prestigious estate area. The 14-room residence offers 7,500 square feet of living space and showcases timeless architecture and exceptional craftsmanship. Set atop a private drive marked by stately stone pillars, the home is surrounded by sweeping lawns, specimen trees, perennial gardens, and a tranquil man-made freshwater creek. An inviting in-ground pool enhances the serene outdoor setting. Inside are six spacious bedrooms, four full baths, and two half baths, including a luxurious primary suite with a spa-like bath. Elegant formal rooms flow seamlessly into comfortable living areas, ideal for both grand entertaining and everyday living.Offering rare privacy with exceptional convenience, this distinguished property is located less than five miles from Back Bay.

71 Sears Road, Brookline

Listing courtesy of Listing Agent: Chamberlain Group from Listing Office: Coldwell Banker Realty - Brookline.

$3,599,000

6 Beds ⋅ 6 Baths ⋅ 73570431 MLS

This stunning Fisher Hill home is surrounded by spectacular gardens and offers over 5,400 square feet of living space. Featuring 6 bedrooms, 5 full baths, and 1 half bath, the home welcomes you with a expansive foyer and curved staircase. The warm and inviting living room boasts floor-to-ceiling windows, a fireplace, and French doors opening to the loggia. The dining room features a fireplace and bowed window overlooking the gardens. An expansive eat-in kitchen includes a center island and upholstered seating area. A bookshelf lined family room and half bath complete the first floor.Upstairs, the grand primary suite offers a walk-in closet, en-suite bath, and shared balcony with the second bedroom. There is a second bedroom on this floor that also includes an en-suite bath and the additional additional bedrooms share a faull bath. The third floor provides extra bedrooms and ideal home office space plus there is a full bath on this floor. The third floor also offers a large walk-in closet that is perfect for additional storage..Additional highlights include a finished basement with exercise room, office, and full bath, plus a two-car garage and beautifully landscaped yard and stone patio. Ideally located for easy access to Washington Square and the C and D line of the T. Convenient to the Runkle Elementary School, Whole Foods, Trader Joes and the shops and restaurants of Coolidge Corner.

17 Chesham Road, Brookline

Listing courtesy of Listing Agent: Bell | Whitman Group from Listing Office: Compass.

$2,895,000

7 Beds ⋅ 4 Baths ⋅ 73568459 MLS

Beautifully situated at the summit of Aspinwall Hill, this gracious, expansive Victorian home offers unique opportunities for the discerning buyer. Originally a single family, it was reconfigured to two units, with private entrances on opposite sides. The spacious yard is a gardener's delight. The front unit features high ceilings, hardwood floors, moldings, original woodwork, and lovely fireplaces. A foyer opens to the living room with a curved bay window, which leads to the formal dining room, also highlighted by bay windows, and finally to an updated kitchen with a large peninsula, ample wood cabinetry, great pantry space and a laundry area. Two bedrooms plus an updated full bathroom complete this level. Upstairs is a large primary bedroom, graced by a curved bay window, with a bright adjoining sitting room offering excellent closet space. Also on this level are another bedroom and an updated full bathroom, with a pristine soaking tub. The second unit offers an eat-in kitchen with 2 adjoining pantries, living room, and unique reading nook, plus 1/2 bath on one level, and 3 bedrooms plus a full bathroom on the upper level. Generous storage space throughout both units. Recently renovated Schick Park is very close by, as well as walking paths. Close proximity to Runkle School and Brookline High. Also nearby are shops, restaurants, public transportation, Star Market and Whole Foods.

71 Addington Rd, Brookline

Listing courtesy of Listing Agent: Kate Vicksell from Listing Office: Hammond Residential Real Estate.

$2,200,000

9 Beds ⋅ 3 Baths ⋅ 73568321 MLS

Calling all investors, developers, and owner-occupants! Introducing 26 Parkway Road, a rare and highly desirable 3-family brick building on a prominent corner lot in Brookline, complete with pre-existing off-street parking. Each of the three spacious units features 3 bedrooms, 1 bathroom, in-unit laundry hookups, and its own private enclosed porch, offering an exceptional combination of space, privacy, and rental appeal. Located minutes from the Longwood Medical Area and some of the world’s leading hospitals and universities, including Harvard Medical School, Boston University, Boston College, Northeastern University, and Simmons University. Enjoy unparalleled access to the Green Line, major roadways, restaurants, shopping, parks, and everything Brookline and Boston have to offer. A rare opportunity to acquire a multifamily asset in a premier location with strong rental potential and significant long-term upside. Properties like this rarely come to market—don’t miss it.

26 Parkway Road, Brookline

Listing courtesy of Listing Agent: Dan Rosenthal from Listing Office: Rise Signature Homes.

$2,895,000

7 Beds ⋅ 4 Baths ⋅ 73568175 MLS

Beautifully situated at the summit of Aspinwall Hill, this gracious, expansive Victorian home offers unique opportunities for the discerning buyer. Originally a single family, it was reconfigured to two units, with private entrances on opposite sides. The spacious yard is a gardener's delight. The front unit features high ceilings, hardwood floors, moldings, original woodwork, and lovely fireplaces. A foyer opens to the living room with a curved bay window, which leads to the formal dining room, also highlighted by bay windows, and finally to an updated kitchen with a large peninsula, ample wood cabinetry, great pantry space and a laundry area. Two bedrooms plus an updated full bathroom complete this level. Upstairs is a large primary bedroom, graced by a curved bay window, with a bright adjoining sitting room offering excellent closet space. Also on this level are another bedroom and an updated full bathroom, with a pristine soaking tub. The second unit offers an eat-in kitchen with 2 adjoining pantries, living room, and unique reading nook, plus 1/2 bath on one level, and 3 bedrooms plus a full bathroom on the upper level. Generous storage space throughout both units. Recently renovated Schick Park is very close by, as well as walking paths. Close proximity to Runkle School and Brookline High. Also nearby are shops, restaurants, public transportation, Star Market and Whole Foods.

71 Addington Rd, Brookline

Listing courtesy of Listing Agent: Kate Vicksell from Listing Office: Hammond Residential Real Estate.

$3,900,000

6 Beds ⋅ 5 Baths ⋅ 73566334 MLS

Rarely does a pristinely renovated single family home in A+ Coolidge Corner location offer a combination of space, flexibility and functionality for long term needs, peaceful outdoor living space, abundant parking, and unlimited potential. This classic colonial has curb appeal,6 bedrooms, 4.5 baths and 4060 Sq feet finished space. 7016 sq foot lot in T5 zone. 4 levels of comfortable living with room for extended family. 90 foot driveway with wide turn around. 4 car garage plus parking for 3 additional NON tandem spaces - major bonus in Brookline. Landscape graced with beautiful cherry tree. Fenced in yard offering tranquility, unusual plantings, trees, plus fire pit for gatherings. 900 sq feet by right ADU potential development in carriage house. Also, a private entry in law/office suite or rental unit for generating income. Kitchen boasts white quartz with wonderful breakfast area, lots of storage & state of art new appliances. New tiled bathrooms. All new Lennox HVAC systems, hot water tank, and rubber roof. Multiple heating zones. Refurbished slate roof, newly painted interior, mudroom, recessed lighting, refinished hardwood flooring, updated electric, and gas fireplace. Custom sauna for well being. 2 sets of washer dryers. Every daily convenience outside your door. Close to Longwood medical, Cambridge pharma and biotech. Excellent public and private schools nearby. 3000 sq ft expansion potential. Wired ring security system. Explore diverse ethnic restaurants nearby surrounded by arts and entertainment. Easy living. Endless possibilities for this unique offering, an expansive and multigenerational home for future years of enjoyment. Area rich in history. Beautiful tree lined property and area.

38 Fuller Street, Brookline

Listing courtesy of Listing Agent: Stacey Steck from Listing Office: Gibson Sotheby's International Realty.

$6,495,000

9 Beds ⋅ 9 Baths ⋅ 73564889 MLS

This 9-bedroom, 6 full/3 half bath residence spans 8,619 sq ft, blending timeless architectural character with thoughtful modern updates throughout. A stunning 2024-renovated kitchen with fireplace and radiant heated flooring anchors the home, complemented by a newly enclosed breezeway, cozy breakfast nook and gracious dining room with double French doors. All-new Pella windows enhance the home throughout, while refinished hardwood floors and fresh paint create a beautifully refreshed interior. Designed with both everyday living and entertaining in mind, the home features a sunken living room with direct exterior access to the solarium and screened porch, creating a seamless connection between the interior and surrounding grounds. The greenhouse conservatory has been completely reimagined with honed absolute black stone, new tile flooring, and a custom fountain, offering a truly distinctive space within the home. Generous bedroom suites and thoughtfully updated baths provide privacy and comfort throughout. A private-entrance, attached in-law/au pair suite offers exceptional flexibility for guests or staff, while an epoxy-finished garage round out the home's modern improvements. Outdoors, a stone patio extends the home's entertaining space onto the expansive, level grounds, with the rare opportunity to add a pool and create a truly exceptional indoor-outdoor setting. Minutes to the Longwood Medical Area (8–10 min), Fenway (10–15 min), Back Bay (15–20 min), and Logan Airport (20 min), with Brookline Reservoir, Fisher Hill Reservoir Park, Larz Anderson Park, and the Emerald Necklace all nearby. A short drive delivers Chestnut Hill's premier shopping, dining, Equinox, and Wegmans. A once-in-a-generation offering.

372 Warren St, Brookline

Listing courtesy of Listing Agent: Gabrielle Russo from Listing Office: Coldwell Banker Realty - Boston.

$12,000

7 Beds ⋅ 4 Baths ⋅ 73563392 MLS

This thoughtfully renovated carriage house is perfect for those who need to be near Longwood or close to the city. This luxurious single-family home can be delivered furnished or unfurnished. Located in the Longwood area, with many options for guests to visit or an in-law suite with exterior access, this home offers endless possibilities. Stroll to the T or enjoy access to local parks and conservation areas. Nearby hospitals or local universities make this an easy choice for professionals. Easy access to downtown and local amenities makes this the right choice for a discerning occupant. Comes with two off-street parking spaces and in-home laundry. Easy to show and will be delivered 9/1.

259 Kent Unit R, Brookline

Listing courtesy of Listing Agent: Sarah Rodewald from Listing Office: SR Realty.

$2,500,000

7 Beds ⋅ 4 Baths ⋅ 73562477 MLS

Owner is Broker.

103-105 Colbourne Crescent, Brookline

Listing courtesy of Listing Agent: Aaron Adler from Listing Office: Appraisals Unlimited, Inc.

$3,700,000

6 Beds ⋅ 5 Baths ⋅ 73561991 MLS

292 Clinton Road is a timeless Victorian residence, built in 1892 and prominently situated in Brookline’s Fisher Hill neighborhood. Rich in architectural detail, this meticulous home has been thoughtfully updated while preserving elegance and craftsmanship. A welcoming front porch leads to a gracious foyer with soaring ceilings, abundant natural light and original woodwork. Designed for grand entertaining and comfortable everyday living, the first floor features a fireplaced living room, dining room, family room with a bay window, a renovated Chef’s kitchen, pantry, mudroom and half bath. A stunning staircase leads to the second level, with a charming sun-drenched landing and a wall of glass. The primary suite offers a custom walk-in closet, and renovated en-suite bath, accompanied by two additional good-sized bedrooms with en-suite baths and a second-floor laundry room. The third floor offers flexibility with three additional bedrooms, a full bath, and a spacious room ideal for a home office.

292 Clinton Rd, Brookline

Listing courtesy of Listing Agent: Luan White from Listing Office: Coldwell Banker Realty - Brookline.

$3,175,000

9 Beds ⋅ 5 Baths ⋅ 73561389 MLS

Blue-Chip Coolidge Corner mixed-use opportunity. 1343 Beacon Street sits in the middle of one of Greater Boston's strongest and most walkable retail corridors, with the Green Line C branch at the door and a direct ride to Longwood Medical Area, Fenway, BU and downtown Boston. The immediate stretch of Beacon and Harvard Streets is anchored by Trader Joe's, the Coolidge Corner Theatre, banks, cafes and long-established neighborhood retail, generating steady foot traffic day and night in a submarket where storefront vacancy has long been low. The property consists of three residential apartments over a ground-floor commercial space: three 3-bedroom/1-bath units plus ground floor retail. Residential units are recently updated and leased through 9/1/27. Commercial space is delivered VACANT, allowing an owner-user to occupy or an investor to lease it at current market terms. A rare chance to own a well-located mixed-use asset with in-place residential cash flow, immediate upside in the ground-floor commercial space, and long-term land value on Beacon Street.

1343 Beacon St, Brookline

Listing courtesy of Listing Agent: Jacob Simmons from Listing Office: City Realty Group.

$3,195,000

9 Beds ⋅ 5 Baths ⋅ 73561142 MLS

RENOVATED Side-by-Side 2-FAMILY in BROOKLINE near Washington Square. Townhome Style Layouts, Each Unit has a Private Entry & Each home enjoys Private Outdoor Space, Deck + Terrace + Patio. Central A/C with separate HVAC. The Large DRIVEWAY, holds 3 Car Parking in Tandem. Strong Rental History! One Unit (#37) is 1600SF, 4BR/2BA, located on the right side and can be "Owner Occupied" while you collect rent ($7,225/month) next door at #39 w/Lease thru 8/31/27. That Penthouse Duplex is Spacious & Renovated with 5 Bedrooms/3 Bathrooms. The Living/Dining showcase a Wall of Windows, overlooking a Tree-lined Beaconsfield Road. Each room is Bright & Sundrenched across 3000 Square Feet. The finishes throughout are Condo-Quality! Beautiful Hardwood Floors, Central A/C, In-Unit Washer/Dryer. Entering the Kitchen, The Delighted Chef in YOU feels at home with a Gas Cooking & High-End Appliances like VIKING + SUB-ZERO. On the left side, #39 has generously-sized Bedrooms with a WOW Primary Suite --Walk in Closet--Primary Bathroom. Cherry Wood Cabinets surround a Double Vanity. The Cherry on Top? The Vanity has Custom Storage on ALL sides...Left | Right | Center...PRIME LOCATION with Access to Washington Square's Restaurants, Botique Shops and Star Market. Just minutes to the Beaconsfield Green Line (T) station, D Line + C Line. Only 10 min walk to Brookline High School or The Brookline Reservoir. Beaconsfield is a side street, making this an exceptional Investment Opportunity.

37-39 Beaconsfield Road, Brookline

Listing courtesy of Listing Agent: Collin Bray from Listing Office: Century 21 Cityside.

$1,800,000

10 Beds ⋅ 4 Baths ⋅ 73559809 MLS

Investors, take note! Don't miss this exceptional opportunity to own a three-family property in one of Brookline's most sought-after locations. Situated near Brookline Village, this property is just a 12-minute walk to the Green Line, providing convenient access to Fenway, Downtown Boston, and beyond. The MBTA Route 60 bus to the Longwood Medical Area is just steps from the front door.Enjoy a highly walkable neighborhood with easy access to grocery stores, restaurants, parks, walking trails, and all the amenities that make Brookline such a desirable place to live.The rear porches offer beautiful city views, and with modern updates, this classic property has the potential to truly shine! Large driveway accommodates multiple cars for easy off street parking. Enjoy the ample yard space for grilling, bonfires, or just taking in the fresh air! Located in a community renowned for its exceptional schools, vibrant neighborhoods, and unbeatable location, this is an investment opportunity you won't want to miss.

86 Chestnut St, Brookline

Listing courtesy of Listing Agent: Sarah McIntyre from Listing Office: Red Tree Real Estate.

$15,750,000

79 Beds ⋅ 31 Baths ⋅ 73554361 MLS

Rare opportunity to acquire a generational asset in the heart of Washington Sq., Brookline. Just a stone’s throw away from Beacon St. – 10-24 University Rd. is positioned alongside one of the most transit-oriented throughfares in/around Greater Boston, providing immediate MBTA access to major universities, like BU, Northeastern and Wentworth, the Longwood Medical Area and the many tech and engineering hubs in Kenmore Sq./Downtown Boston. Addressed as 10-12, 16-18 and 22-24 University Rd., the offering consists of three (3) 7-unit buildings and eleven (11) surface level parking spaces on contiguous parcels spanning 23,479 sq./ft. in cumulative lot size. Gross building area within the shells of all three buildings amounts to 57,928 sq./ft. but twenty-one (21) residential units comprise 35,512 sq./ft. of living space, with eighteen (18) 4-5 bedroom dwellings across the first, second and third levels and three (3) 1-2 bedroom dwellings on the garden levels. While substantial value-add potential can be achieved by preserving the current building designs, additional opportunities may also exist by tapping into unutilized space on the fourth floors/garden levels, rearranging floorplans and/or increasing the total unit count.

10-24 University Rd., Brookline

Listing courtesy of Listing Agent: Joe Danisch from Listing Office: Coelho Realty Group LLC.

$9,700

6 Beds ⋅ 4 Baths ⋅ 73537477 MLS

Recently renovated three-level Victorian-style single-family home located on picturesque, tree-lined Davis Avenue in one of Brookline’s most desirable neighborhoods. This spacious residence offers 6 bedrooms, a dedicated home office, and 4 full bathrooms. An elegant entryway showcases original natural woodwork, classic architectural details, and gleaming hardwood floors throughout.The thoughtfully designed chef’s kitchen features Wolf appliances, gas cooking, a professional-grade hood vent, stone countertops, and abundant custom cabinetry. Generously sized bedrooms on the second and third floors offer custom closets and exceptional natural light. The luxurious primary bath is European-inspired, featuring a walk-in shower and BainUltra soaking tub.Additional amenities include central air conditioning, in-unit laundry, and two off-street parking spaces. Ideally situated near Pierce School, Brookline High School, Brookline Village, parks, and playgrounds. Just steps from the Green Line.

191 Davis Ave, Brookline

Listing courtesy of Listing Agent: Jing Tu from Listing Office: Coldwell Banker Realty - Cambridge.

$14,995,000

6 Beds ⋅ 8 Baths ⋅ 73537408 MLS

Designed to be admired and built to be enjoyed, 33 Sears Rd is a custom residence set on 1.6 acres of manicured, private grounds. The home makes an immediate statement with a grand two-story foyer that introduces soaring ceilings, refined detailing, and beautifully scaled living spaces throughout. Built by one of Boston's premier female builders, the craftsmanship is evident in every threshold, finish, and room proportion. The open-concept main level was thoughtfully designed to offer grand room sizes without sacrificing warmth. A custom chef's kitchen appointed with top-tier appliances anchors the heart of the home, complemented by a separate, fully equipped prep kitchen. The primary suite features a dramatic two-story walk-in closet, a rare offering that quietly separates this residence from others on the market. Elevator infrastructure is already in place. Outdoor living is equally compelling, w/ ample acreage to accommodate a future pool, sport court, or other lifestyle amenities.

33 Sears Rd, Brookline

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.

$11,750,000

6 Beds ⋅ 9 Baths ⋅ 73536353 MLS

A rare opportunity to reimagine and create a $20+M compound in Brookline, set on two private acres in the coveted estate area. Conceived by an award-winning architect, the proposed design masterfully blends timeless elegance and exceptional craftsmanship with the features most desired for modern living soaring ceilings, abundant natural light, clean architectural lines, and a thoughtfully designed floor plan ideal for both grand entertaining and everyday comfort. The proposed plans showcase an expansive open-concept kitchen and family room with a dramatic cathedral ceiling, elegant formal living and dining rooms, spacious library, a screened porch, a gracious 1st floor bedroom, and an exceptional 2nd floor primary suite. Additional customization options include an elevator servicing all levels, a golf simulator, and a swimming pool. Offering rare privacy with exceptional convenience, this distinguished property is located less than five miles from Back Bay

Sears Road, Brookline

Listing courtesy of Listing Agent: Chamberlain Group from Listing Office: Coldwell Banker Realty - Brookline.

$5,500,000

12 Beds ⋅ 8 Baths ⋅ 73534622 MLS

Rare development opportunity in the heart of Brookline's coveted Washington Square neighborhood. Situated on University Road, 97 and 101-103 University are comprised of two abutting multifamily lots totaling 12,219 SF (approximately 6,000 SF each), with the ability to build three residential units on each lot by right. 6 Units total. OR ZBA-approved plans for a 9 Unit Development... past demo stay. Developers, investors, and end-users alike will appreciate the flexibility to develop the parcels separately or explore combining the lots for a larger-scale project. This property is offering a rare chance to capitalize on one of Greater Boston's most desirable and supply-constrained residential markets. No representations made by seller; buyer to perform their own due diligence. Email or Text me for more details.

97-103 University Rd, Brookline

Listing courtesy of Listing Agent: Eric Tam from Listing Office: Compass.

$8,200,000

6 Beds ⋅ 9 Baths ⋅ 73526856 MLS

Set on over 1.2 acres with a 1.62-acre experience via a neighboring easement, this exceptional Chestnut Hill estate offers a tranquil oasis on one of the area’s most coveted and secluded streets. Originally built in 1900 and thoughtfully renovated over time, the residence spans more than 9,300 square feet with six bedrooms, six full bathrooms, and three half bathrooms. Its richly detailed living spaces were designed for both elegant entertaining and everyday comfort. Gracious formal rooms, soaring ceilings, and exquisite millwork overlook beautifully landscaped grounds featuring a heated, in-ground pool, a basketball court, and ample parking. Once home to Alvan T. Fuller, the 50th Governor of Massachusetts, the property carries remarkable historic provenance. The grounds were originally designed by Frederick Law Olmsted, further contributing to the property’s timeless character. This is a rare opportunity to own a historic estate of this scale in an unbeatable location.

40 Singletree Rd, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$35,000

7 Beds ⋅ 9 Baths ⋅ 73524131 MLS

Set on nearly an acre within Brookline’s coveted Estate Section, this extraordinary 2015-built residence offers a rare blend of privacy, scale, & exceptional construction rarely found in today’s market. Spanning nearly 8,000 sq ft including a finished lower level, the home features solid mahogany floors,marble baths, custom granite stonework, 7 bedrooms, 9 bathrooms, a steam room, and multiple fireplaces including a striking outdoor granite fireplace on the covered rear deck for year-round entertaining. A fully restored original Carriage House provides two additional floors ideal for a gym, studio, or guest quarters, while a separate private office or nanny suite offers its own entrance. Built to an impressive standard with geothermal heating and cooling across six zones, radiant floor heating, Andersen Architectural Series windows, 600-amp electrical service, EV charging, and extensive CAT5 wiring. Minutes to The Country Club, Dexter Southfield, Larz Anderson Park, and downtown Boston

75 A Goddard Avenue Unit 75, Brookline

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.

$1,299,000

7 Beds ⋅ 2 Baths ⋅ 73518618 MLS

Recently renovated! Come and check it out! Incredible Brookline Village location, convenient to the Longwood Medical Area and the street with the historic Dutch House. This stunning brick row house duplex offers the flexibility to be utilized as an investment or as one single unit! First floor features 3 bedrooms,1-bathroom, gorgeous high ceilings, ample natural light, lovely original hardwood floors throughout, exposed brick, and a thoughtful layout. The condo has so much character with built-in bookshelves in the hallways, French doors leading to the formal dining room, an updated kitchen, and a bathroom. Off the kitchen is a back staircase leading to the finished in-law suite, which has 4 bedrooms, an office, a full kitchen, a living room, and a full 2nd bathroom. The property also has a private patio with a private yard and a large private deck perfect for entertaining. Property is conveniently located near Greenline trains, Brookline Ave buses, and bike paths, with an easy walk to the Longwood Medical Area/Emerald Necklace

23 Netherlands Rd Unit 1, Brookline

Listing courtesy of Listing Agent: Vena Priestly from Listing Office: Rise Signature Homes.

$2,399,000

6 Beds ⋅ 3 Baths ⋅ 73515119 MLS

A turnkey investment or owner-occupant gem in Brookline’s highly sought after area.This mixed-use property features two spacious 3-bedroom residential units over a established commercial restaurant space with consistent income .Perfect for the savvy investor seeking stable yields or a homeowner looking to offset their mortgage with commercial and residential rent.This property combines classic Brookline charm with an unbeatable location and functional upgrades.Don't miss this high-performing asset.Two 1513 sq ft. residential units are fully furnished with hardwood floors, washer and dryer as well as an outdoor porch.The first floor is a family dining restaurant with a strong lease and great payment history.There is dedicated storage for all units in the basement.Plenty of recreational opportunities nearby including the newly remodeled Robinson Playground across the street.Very easy MBTA access and close proximity to the Boston medical area make this a prime location.Paved parking for 3The exterior has been newly painted and price dropped!

293 Cypress St, Brookline

Listing courtesy of Listing Agent: John J. Canney from Listing Office: John J. Canney.

$14,850,000

6 Beds ⋅ 8 Baths ⋅ 73507123 MLS

Privately set off Warren St, this exceptional Brookline estate spans over 3.6 acres of beautifully landscaped grounds and over 9,000 SF across four levels, with 6 bedrooms, 6 full and 2 half baths. A striking entry with a sweeping staircase leads to expansive, light-filled living and entertaining spaces rich with charm and detailed moldings. The main level features a mix of formal and informal spaces, multiple offices, and a beautifully designed kitchen with high-end appliances, custom cabinetry, and an eat-in dining area overlooking the grounds. Upstairs, the primary suite includes a luxurious bath and generous dressing rooms, along with five additional bedrooms, family room, and laundry. The serene third floor offers flexible space for a gym, studio, or additional living. Outside, the grounds are unmatched - a pond, patios, firepit, and hot tub perfect for entertaining and everyday living. A one-of-a-kind offering in one of Brookline's most sought-after neighborhoods.

280 Warren St, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$8,995,000

7 Beds ⋅ 6 Baths ⋅ 73496969 MLS

Discover 39 Worthington Road in Brookline's coveted Cottage Farm neighborhood. This fully renovated masterpiece boasts 7 bedrooms and 5.5 bathrooms with impeccable craftsmanship and attention to detail. The interior, designed by a renowned interior designer has been featured in various publications. Wonderful spaces for entertaining and comfortable living include a large custom-designed chef's kitchen open to a gracious family room with custom millwork built-ins along with a large library with over 12' ceilings. There is a luxurious primary suite with a spa-like bath, walk-in closets, a sun-filled study, & access to a terrace. The lower level includes a gym, playroom, and more. Nestled on a double, extra-large expansive landscaped lot complete with a hockey rink (and equipment) and full outdoor kitchen, privacy and serenity, and indoor/outdoor living abound. The ideal setting and location that defines urban-suburban living close to all Boston/Cambridge/Brookline has to offer.

39 Worthington Rd, Brookline

Listing courtesy of Listing Agent: Rachel Goldman from Listing Office: MGS Group Real Estate LTD.

$7,500,000

6 Beds ⋅ 8 Baths ⋅ 73487838 MLS

A rare find in Brookline, this property offers privacy and tranquility on a secluded lot adjacent to Sargent Estates. Spanning three finished levels plus a lower level, the home features 6 bedrooms and 6 full and 2 half baths, with meticulous craftsmanship and striking architectural details throughout. A grand rotunda entry leads to a chef’s kitchen, expansive living and dining rooms, family room, and mudroom. The second floor includes three bedroom suites, each with its own bath, plus two office spaces. The third floor offers two additional bedroom suites, while the lower level includes a sixth suite, gym, large family room, and laundry. Surrounded by mature landscaping and set well back from the street, the property boasts a pool, hot tub, sauna, outdoor fireplace, pizza oven, and full outdoor kitchen—an exceptional setting for both relaxation and entertaining. Not to be missed!

1 Chestnut Place, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$6,800,000

7 Beds ⋅ 9 Baths ⋅ 73486175 MLS

Set on nearly an acre within Brookline’s coveted Estate Section, this extraordinary 2015-built residence offers a rare blend of privacy, scale, & exceptional construction rarely found in today’s market. Spanning nearly 8,000 sq ft including a finished lower level, the home features solid mahogany floors,marble baths, custom granite stonework, 7 bedrooms, 9 bathrooms, a steam room, and multiple fireplaces including a striking outdoor granite fireplace on the covered rear deck for year-round entertaining. A fully restored original Carriage House provides two additional floors ideal for a gym, studio, or guest quarters, while a separate private office or nanny suite offers its own entrance. Built to an impressive standard with geothermal heating and cooling across six zones, radiant floor heating, Andersen Architectural Series windows, 600-amp electrical service, EV charging, and extensive CAT5 wiring. Minutes to The Country Club, Dexter Southfield, Larz Anderson Park, and downtown Boston

75 Goddard Avenue, Brookline

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.

$9,500,000

7 Beds ⋅ 8 Baths ⋅ 73485408 MLS

Magnificent estate on one of Brookline’s most beautiful residential streets, blending timeless architecture with modern luxury. Expansive first floor features elegant period details, grand entertaining rooms, an impressive foyer, custom chef’s kitchen, and spacious family room, with a covered porch and large deck extending the living space outdoors. The home offers a palatial primary suite with fireplace, multiple closets, & a spa-like bath, along with additional en-suite bedrooms and a third-floor recreation space.The fully finished lower level includes a kitchen, gym, theater, recreation room, additional bedrooms, and full bath. Additional highlights include radiant heated floors, smart home technology, and an oversized double-depth garage accommodating up to six cars. Set on nearly one acre of beautifully landscaped grounds w/ a swimming pool, clay tennis court, and heated driveway and walkways for snowmelt. An exceptional residence offering luxury, privacy, extraordinary amenities.

355 Buckminster Road, Brookline

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.

$16,000,000

6 Beds ⋅ 8 Baths ⋅ 73480812 MLS

This spectacular residence, set on 4.5 acres in the prestigious Brookline Estate area, has been renovated and is surrounded by private, scenic landscapes. The interior, distinguished by its grandeur and elegance, is adorned with intricate period details, beautiful woodwork, and bright spacious rooms. The grand 13 rooms include a double living room with picturesque views of the gorgeous, expansive grounds. There are 6 bedrooms, one of which is the luxurious primary suite. The meticulously designed grounds feature several unique amenities, including a stunning terrace patio expanding the length of the home, an in-ground swimming pool with fountain and whirlpool artfully integrated with a stone cliff, fully equipped cabana, koi pond, private tennis court, putting green, and magnificent hardscaping. The property also has a three-bedroom cottage and a two-bedroom unit above the free-standing garage. Near fine shops, restaurants, and Downtown Boston.

63 Goddard Avenue, Brookline

Listing courtesy of Listing Agent: Debby Belt from Listing Office: Hammond Residential Real Estate.

$8,995,000

6 Beds ⋅ 7 Baths ⋅ 73479457 MLS

Exquisite in every detail, this magnificent brick Georgian boasts modern style design, suitable for grand scale entertaining & comfortable family living. A large, elegant foyer w/sweeping staircase & venetian plaster walls, opens to an elegant living room w/fireplace. A sunroom, just off the foyer, offers spectacular views of the level, acre+ lot w/ frontage on Cramond Street. There is a majestic dining room w/acoustic padded walls & a handsome family room w/custom cabinetry. The fully renovated chef’s kitchen features a center island, butler’s pantry & dining nook—truly exceptional w/top-grade appliances. The 2nd level has a luxurious primary suite w/fireplace & spa-like bath. There are 3 additional bedrooms, 3 full baths, an office & a laundry room on this level. The 3rd floor offers 2 additional bedrooms & a full bath. The lower level has a large media room, gym room, full bath, 2nd laundry room, mudroom & access to the 2-car garage. Easy access to highways, schools & airport.

188 Heath St, Brookline

Listing courtesy of Listing Agent: The Kennedy Lynch Team from Listing Office: Hammond Residential Real Estate.

$4,800,000

6 Beds ⋅ 7 Baths ⋅ 73466199 MLS

Over the past century, The Loring-Atherton House has been owned by just two families. Now, this distinguished Cottage Farm residence presents a rare opportunity for its next owner to thoughtfully reinterpret it for a new era. Set on a prominent corner lot in the heart of Brookline’s Cottage Farm Historic District, the residence is an exceptional example of Georgian Revival architecture. Its stately brick exterior is defined by a slate roofline, dormer windows, tall chimneys and a classically detailed entrance crowned by an arched fanlight. At the rear, a broad brick terrace, graceful curved staircases and a multi-paned bay overlook the mature, tree-canopied grounds. Inside, the home reveals an extraordinary collection of architectural details. A dramatic great room features a soaring exposed timber ceiling, hand-painted decorative friezes, richly paneled walls, built-in bookcases and window seating, and a substantial marble fireplace. Elsewhere, a beautifully crafted wood staircase, patterned tile floors, ornamental ironwork, additional fireplaces and a mural-lined library speak to the artistry and character carried throughout the residence. Together, these elements provide a compelling architectural language from which something entirely personal can be created. Currently offering six bedrooms and six and a half bathrooms across approximately 8,326 square feet of finished living space, the property encompasses more than 10,000 square feet of finished and unfinished space in total. The opportunity is not simply to restore what was, but to consider how its most distinctive elements can inform what comes next, creating a home that feels relevant to the present while remaining connected to its remarkable history. Directly across from Mason Square Park and moments from the Longwood Medical Area, Fenway, Boston University, leading schools and many of the region’s finest cultural and green spaces, 180 Ivy Street offers the architectural character and greenery of Brookline while keeping Back Bay, downtown Boston, Cambridge and Harvard University all within easy reach. More than a significant address, it is an opportunity to carry forward a century-long legacy while defining its next era.

180 Ivy St, Brookline

Listing courtesy of Listing Agent: Ricardo Rodriguez & Associates Group from Listing Office: Coldwell Banker Realty - Boston.

$16,980,000

7 Beds ⋅ 11 Baths ⋅ 73445544 MLS

Introducing Paine Estate, a grand Georgian Revival architectural treasure located in the highly coveted Chestnut Hill neighborhood of Brookline. This outstanding property has been extensively renovated, now combining traditional style and modern amenities with a thoughtful floor plan ideal for comfortable family living and grand entertaining. Exceptional features include a grand entry hall, elegant formal sunken living room overlooking the picturesque gardens, fireplaced dining room, gourmet chef's kitchen, family room, handsome wood paneled library and an expansive great room. 6 bedrooms include the luxurious primary suite complete with separate bathrooms and dressing rooms and balcony. Additional features include a mudroom, exercise/club room, au-pair suite and wine cellar. This majestic home is surrounded by over 2 acres of beautifully landscaped grounds featuring an outside kitchen and dining area, a formal parterre garden and plunge pool. Magnificent opportunity not to be missed!

1014 Boylston Street, Brookline

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.

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